Title

Efficient synthesis and reactions of 1,2-dipyrrolylethynes

Document Type

Article

Publication Date

1-1-2011

Abstract

Various dipyrroles possess important motifs for construction of pyrrole-containing pigments. A series of 1,2-dipyrrolylethynes (4ad) has been efficiently synthesized using an improved one-pot double Sonagashira coupling from trimethylsilylethyne and various 2-iodopyrroles. The resulting 1,2-dipyrrolylethynes were further transformed into novel indolyl-, ethenyl- and carboranyl-dipyrroles (57) using the Larock indole synthesis, stereoselective catalytic hydrogenation, or B10H14. Indolyl-dipyrroles were found to selectively bind fluoride ions using one pyrrolic and the indolyl NHs, whereas the carboranyl- and ethenyl-dipyrroles are potentially valuable precursors for the synthesis of porphyrin isomers and expanded pigments. © 2011 World Scientific Publishing Company.

Publication Source (Journal or Book title)

Journal of Porphyrins and Phthalocyanines

First Page

412

Last Page

420

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